178306-47-3

Basic information

• Product Name: Benzenepropanoic acid,a-hydroxy-b-methoxy-b-phenyl-,methyl ester
• Synonyms: Benzenepropanoic acid,a-hydroxy-b-methoxy-b-phenyl-,methyl ester;2-Hydroxy-3-methoxy-3,3-diphenylpropanoic acid methyl ester;Methyl 2-hydroxy-3-methoxy-3,3-diphenylpropanoate;α-Hydroxy-β-Methoxy-β-phenyl-benzenepropanoic Acid Methyl Ester;Ambrisentan PI-4;ALST-01;2-hydroxy-3-methoxy-3;3-diphenylpropanoic acid methyl ester
• CAS NO: 178306-47-3
• Molecular Formula: C₁₇H₁₈O₄
• Molecular Weight: 286.32
• EINECS: 1806241-263-5
• Product Categories: Drug Intermediates;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 178306-47-3.mol

Chemical Properties

• Boiling Point: 440.722 °C at 760 mmHg
• Flash Point: 159.393 °C
• Appearance: /
• Density: 1.176
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.56
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Very Slightly)
• PKA: 12.37±0.20(Predicted)
• CAS DataBase Reference: Benzenepropanoic acid,a-hydroxy-b-methoxy-b-phenyl-,methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenepropanoic acid,a-hydroxy-b-methoxy-b-phenyl-,methyl ester(178306-47-3)
• EPA Substance Registry System: Benzenepropanoic acid,a-hydroxy-b-methoxy-b-phenyl-,methyl ester(178306-47-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 178306-47-3(Hazardous Substances Data)

Usage

Uses

Ambrisentan intermediate.

InChI:InChI=1/C17H18O4/c1-20-16(19)15(18)17(21-2,13-9-5-3-6-10-13)14-11-7-4-8-12-14/h3-12,15,18H,1-2H3

Upstream product

• 178306-52-0 (S)-2-hydroxy-3-methoxy-3,3-diphenylpropionic acid 
• 178306-51-9 (S)-2-hydroxy-3-methoxy-3,3-diphenyl propionic acid 
• 119-61-9 benzophenone 
• 96-34-4 methyl chloroacetate 
• 76527-25-8 3,3-diphenyloxirane-2-carboxylic acid methyl ester 
• 67-56-1 methanol 

Downstream Products

• 1025933-19-0 3-Methoxy-2-(4-methyl-pyrimidin-2-yloxy)-3,3-diphenyl-propionic acid methyl ester 
• 178306-52-0 (S)-2-hydroxy-3-methoxy-3,3-diphenylpropionic acid 
• 177036-78-1 (S)-2-hydroxy-3-methoxy-3,3-diphenylpropionic acid methyl ester 
• 177036-94-1 ambrisentan 
• 171714-84-4 darusentan 
• 1106685-61-3 (S)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropionic acid methyl ester 
• 177036-79-2 (S)-methyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionate 
• 1231755-36-4 (S)-2-hydroxy-3-methoxy-3,3-diphenylpropionic acid tertiary butylamine salt 
• 1431363-04-0 methyl 3-methoxy-2-oxo-3,3-diphenylpropionate 
• 1240470-84-1 (S)-methyl-2-(4,6-dimethylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionate 
• 177036-94-1 ambrisentan 
• 178306-45-1 (S)-methyl-2-(4,6-dimethoxypyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionate 
• 178306-46-2 (.S)-2-(4,6-dimethoxypyrimidin-2-yloxy)-3-methoxy-3,3-diphenyl propionic acid 
• 1025849-08-4 3-Methoxy-2-(4-methoxy-6-methyl-pyrimidin-2-yloxy)-3,3-diphenyl-propionic acid methyl ester 

Relevant articles and documents

LC-MS/MS characterization of forced degradation products of ambrisentan: Development and validation of a stability-indicating RP-HPLC method

The current study reports the characterization of degradation products of ambrisentan by liquid chromatography-tandem mass spectrometry, and development and validation of a stability-indicating reversed phase high performance liquid chromatographic method

Synthesis method of 2-hydroxy-3-methoxy-3, 3-diphenyl propionic acid

The invention relates to a synthetic method of 2-hydroxy-3-methoxy-3, 3-diphenyl propionic acid. The invention relates to a preparation method of an ambrisentan key intermediate 2-hydroxy-3-methoxy-3,3-diphenyl propionic acid. According to the preparation

An improved method of preparing Anritsu tezosentan

The invention belongs to the field of chemical synthesis, and discloses an improved method used for preparing ambrisentan. According to the improved method, 2-hydroxy-3-methoxy-3,3-diphenylpropionic ester and 4,6-dimethyl-2-methylsulfonylpyrimidine are su

Process Research for (+)-Ambrisentan, an Endothelin-A Receptor Antagonist

An efficient and robust synthetic route to (+)-ambrisentan ((+)-AMB) was designed by recycling the unwanted isomer from the resolution mother liquors. The racemization of AMB in the absence of either acid or base in the given solvents was reported. The recovery process was developed to produce racemates with purities over 99.5%. The mechanism of the formation of the process-related impurities of (+)-AMB is also discussed in detail. (+)-AMB was obtained in 47% overall yield with >99.5% purity and 99.8% e.e. by chiral resolution with only one recycling of the mother liquors on a 100-g scale without column purification.

METHOD FOR PRODUCING (S)-2-HYDROXYPROPANOIC ACID DERIVATIVE

PROBLEM TO BE SOLVED: To provide a method for producing an (S)-2-hydroxypropanoic acid derivative and ambrisentan having high optical purity in an industrially advantageous manner. SOLUTION: There is provided a method for producing an (S)-2-hydroxypropanoic acid derivative represented by the formula (1a) by reacting an (RS)-2-hydroxypropanoic acid derivative represented by the formula (1) with (S)-(+)-1,2,3,4-tetrahydro-1-naphthylamine to form a diastereomer salt, followed by desalting. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Process for Preparing Ambrisentan

The present invention relates to a method of preparing high purity ambrisentan in a cost-effective and efficient way, and a novel intermediate product used for the method. According to the present invention, optical resolution of 2-hydroxy-3-methoxy-3,3-diphenylpropionic acid can be cost-effectively and efficiently performed using L-prolinamide, and thus crystalline ambrisentan having 99.9% or more of purity and optical purity can be prepared on an industrial scale using the same.COPYRIGHT KIPO 2016

New carboxylic acid derivative, its production and its use

Heterocyclyl-substd. propanoic acids and their derivs., of formula (I), are new. R = formyl, tetrazolyl, nitrile, COOH or a gp. that can be hydrolysed to COOH; X = N or CR14; R2 = H, OH, NH2, alkylamino, dialkylamino, halo, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio; R14 = H or 1-5 C alkyl; R3 = R2 or alkoxyimino; or CR3 + CR14 = 5 or 6 membered alkylene or alkenyl ring (opt. substd. by 1-2 alkyl) in which a methylene can be replaced by O, S, NH or alkylamino; R4, R5 = phenyl or naphthyl (both opt. substd. by one or more halo, NO2, CN, OH, alkyl, haloalkyl, alkoxy, haloalkyloxy, phenoxy, alkylthio, NH2, alkylamine or dialkylamino) or 3-7 C cycloalkyl; or the phenyl or naphthyl gps. are opt. bonded at the O- position (by a bond, CH2, O, S, SO2, ethylene, ethenylene or opt. alkylated amino); R6 = H, 1-8 C alkyl, 2-6 C alkenyl, 3-6 C alkynyl, 3-8 C cycloalkyl (all opt. substd. by 1 or more halo, NO2, CN, alkoxy 3-6 C alkenyloxy, 3-6 C alkynyloxy, alkylthio, haloalkoxy, alkylcarbonyl, alkoxycarbonyl, 3-8 C alkylcarbonylalkyl, alkylamino, dialkylamino, phenyl, Ph or OPh), Ar or Het; Y = S, O or bond; Q = S, O, SO, SO2 or bond; Ph = substd. phenyl, where substits. are halo, NO2, CN, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio; Ar = phenyl or naphthyl (both opt. substd. by 1 or more halo, NO2, CN, OH, NH2, alkylamino, dialkylamino or OCH2CH2O); Het = 5 or 6 membered heteroaromatic with 1-3 N atoms and/or one S or O (opt. substd. by 1-4 halo and/or 1 or 2 alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, phenyl, phenoxy or phenyl carbonyl (where the phenyl is opt. substd. by 1-5 halo and/or 1-3 alkyl, haloalkyl, alkoxy, haloalkoxy and/or alkylthio)); alkyl and alkoxy have 1-4 C unless otherwise stated; provided that R6 is not H when Q = bond.

Process for the Preparation of an Endothelin Receptor Antagonist

The present invention relates to a novel process for the preparation of a compound of formula (I) wherein R is a methyl or methoxy group; to certain novel intermediates prepared in such a process and their use.

IMPROVED PROCESS TO PREPARE S-2-HYDROXY-3-METHOXY-3,3-DIPHENYL PROPIONIC ACID

Disclosed is a process for the preparation of S-2-Hydroxy-3-methoxy-3,3-diphenylpropionic acid (I) the key intermediate for the preparation of Ambrisentan [(+)-2(S)-(4,6-Dimethylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionic acid]. Ambrisentan of the formula (IA) is approved under the trademark "Letairis " by the US Food and Drug Administration for the treatment of Pulmonary artery hypertension(PAH).

Improved Process For The Preparation Of Endothelin Receptor Antagonists

The present invention relates to improved processes for the preparation of Endothelin receptor antagonists, their salts and intermediates.